NPASS Compound

Structure

CID10467 OpenBabel06191715332D 21 23 0 0 0 0 0 0 0 0999 V2000 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 20 1 0 0 0 0 2 4 1 0 0 0 0 2 9 2 0 0 0 0 3 5 2 0 0 0 0 3 9 1 0 0 0 0 4 10 2 0 0 0 0 5 10 1 0 0 0 0 6 11 1 0 0 0 0 6 13 2 0 0 0 0 7 14 2 0 0 0 0 7 15 1 0 0 0 0 8 12 2 0 0 0 0 8 21 1 0 0 0 0 9 12 1 0 0 0 0 10 20 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 16 1 0 0 0 0 13 14 1 0 0 0 0 13 17 1 0 0 0 0 14 18 1 0 0 0 0 15 21 1 0 0 0 0 16 19 2 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	284.07
Volume:	282.482
LogP:	2.885
LogD:	2.65
LogS:	-3.543
# Rotatable Bonds:	2
TPSA:	79.9
# H-Bond Aceptor:	5
# H-Bond Donor:	2
# Rings:	3
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.707
Synthetic Accessibility Score:	2.115
Fsp3:	0.062
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.749
MDCK Permeability:	1.2665713256865274e-05
Pgp-inhibitor:	0.004
Pgp-substrate:	0.952
Human Intestinal Absorption (HIA):	0.005
20% Bioavailability (F20%):	0.009
30% Bioavailability (F30%):	0.775

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.045
Plasma Protein Binding (PPB):	97.02182006835938%
Volume Distribution (VD):	0.427
Pgp-substrate:	3.017012119293213%

ADMET: Metabolism

CYP1A2-inhibitor:	0.944
CYP1A2-substrate:	0.784
CYP2C19-inhibitor:	0.647
CYP2C19-substrate:	0.058
CYP2C9-inhibitor:	0.635
CYP2C9-substrate:	0.894
CYP2D6-inhibitor:	0.848
CYP2D6-substrate:	0.904
CYP3A4-inhibitor:	0.649
CYP3A4-substrate:	0.187

ADMET: Excretion

Clearance (CL):	6.986
Half-life (T1/2):	0.821

ADMET: Toxicity

hERG Blockers:	0.055
Human Hepatotoxicity (H-HT):	0.084
Drug-inuced Liver Injury (DILI):	0.827
AMES Toxicity:	0.18
Rat Oral Acute Toxicity:	0.242
Maximum Recommended Daily Dose:	0.49
Skin Sensitization:	0.927
Carcinogencity:	0.285
Eye Corrosion:	0.006
Eye Irritation:	0.944
Respiratory Toxicity:	0.277

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC10467

Natural Product ID:	NPC10467
*Common Name:**	Formonetin
IUPAC Name:	6,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
Synonyms:	Formonetin
Standard InCHIKey:	GCWOYVFHJDNKIN-UHFFFAOYSA-N
Standard InCHI:	InChI=1S/C16H12O5/c1-20-10-4-2-9(3-5-10)12-8-21-15-7-14(18)13(17)6-11(15)16(12)19/h2-8,17-18H,1H3
SMILES:	COc1ccc(cc1)c1coc2cc(c(cc2c1=O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL239028
PubChem CID:	5281812
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002586] O-methylated isoflavonoids [CHEMONTID:0002606] 4'-O-methylated isoflavonoids [CHEMONTID:0002687] 4'-O-methylisoflavones

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12713396]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16441081]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16675659]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[20022509]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21123068]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21866899]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22074222]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[22074222]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23325115]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[23541646]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	rhizome	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[23867078]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24479468]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	roots	n.a.	n.a.	PMID[24957203]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25445757]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25744461]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26841168]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28140583]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28522265]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29641206]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32196343]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7381508]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1698	Glycyrrhiza inflata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29384	Glycyrrhiza glabra	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7154	Glycyrrhiza uralensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
ED50	1
IC50	6

Activity Type	# Activity
Individual Protein	3
Organism	2
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1119	Individual Protein	Arachidonate 12-lipoxygenase	Homo sapiens	IC50	>	100000.0	nM	PMID[453761]
NPT1139	Individual Protein	Arachidonate 15-lipoxygenase, type II	Homo sapiens	IC50	>	100000.0	nM	PMID[453761]
NPT792	Individual Protein	Arachidonate 15-lipoxygenase	Homo sapiens	IC50	>	100000.0	nM	PMID[453761]
NPT2	Others	Unspecified		IC50	=	50.0	ug.mL-1	PMID[453762]
NPT20	Organism	Candida albicans	Candida albicans	IC50	>	50.0	ug.mL-1	PMID[453762]
NPT85	Organism	Filobasidiella neoformans	Cryptococcus neoformans	IC50	>	50.0	ug.mL-1	PMID[453762]
NPT1	Others	Radical scavenging activity		ED50	=	29.0	uM	PMID[453763]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC10467 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	495
0.1-0.2	2032
0.2-0.3	4969
0.3-0.4	11612
0.4-0.5	5802
0.5-0.6	3911
0.6-0.7	5185
0.7-0.8	4872
0.8-0.85	2105
0.85-0.9	1090
0.9-0.95	542
0.95-1	82

Similarity Score	Similarity Level	Natural Product ID
0.9862	High Similarity	NPC269451
0.9862	High Similarity	NPC181209
0.9862	High Similarity	NPC121522
0.9862	High Similarity	NPC209487
0.9862	High Similarity	NPC216769
0.9862	High Similarity	NPC35763
0.9862	High Similarity	NPC245382
0.9862	High Similarity	NPC291802
0.9862	High Similarity	NPC100263
0.9862	High Similarity	NPC100971
0.9862	High Similarity	NPC131266
0.986	High Similarity	NPC218490
0.9795	High Similarity	NPC124714
0.9793	High Similarity	NPC45291
0.9793	High Similarity	NPC19980
0.9728	High Similarity	NPC39184
0.9724	High Similarity	NPC156953
0.966	High Similarity	NPC250557
0.9658	High Similarity	NPC262623
0.9655	High Similarity	NPC40290
0.9655	High Similarity	NPC142876
0.9655	High Similarity	NPC69430
0.9655	High Similarity	NPC195763
0.9655	High Similarity	NPC333691
0.9655	High Similarity	NPC264550
0.9655	High Similarity	NPC200060
0.9655	High Similarity	NPC264289
0.9655	High Similarity	NPC139293
0.9595	High Similarity	NPC134287
0.9595	High Similarity	NPC130589
0.9589	High Similarity	NPC239363
0.9589	High Similarity	NPC184136
0.9586	High Similarity	NPC80710
0.9586	High Similarity	NPC183655
0.9586	High Similarity	NPC139364
0.9586	High Similarity	NPC254702
0.9586	High Similarity	NPC287395
0.9586	High Similarity	NPC203747
0.9586	High Similarity	NPC194653
0.958	High Similarity	NPC38065
0.958	High Similarity	NPC242893
0.9521	High Similarity	NPC92722
0.9521	High Similarity	NPC38545
0.9521	High Similarity	NPC171916
0.9521	High Similarity	NPC102003
0.9517	High Similarity	NPC125449
0.9517	High Similarity	NPC188074
0.951	High Similarity	NPC287722
0.9467	High Similarity	NPC99597
0.9467	High Similarity	NPC210084
0.9467	High Similarity	NPC78103
0.9463	High Similarity	NPC213622
0.9463	High Similarity	NPC20830
0.9463	High Similarity	NPC2928
0.9463	High Similarity	NPC256612
0.9459	High Similarity	NPC120163
0.9459	High Similarity	NPC83508
0.9459	High Similarity	NPC275836
0.9459	High Similarity	NPC241498
0.9459	High Similarity	NPC301323
0.9459	High Similarity	NPC212678
0.9459	High Similarity	NPC293183
0.9459	High Similarity	NPC162313
0.9459	High Similarity	NPC323626
0.9459	High Similarity	NPC131624
0.9459	High Similarity	NPC57030
0.9459	High Similarity	NPC25270
0.9459	High Similarity	NPC222830
0.9459	High Similarity	NPC156222
0.9459	High Similarity	NPC239128
0.9459	High Similarity	NPC256283
0.9459	High Similarity	NPC187498
0.9459	High Similarity	NPC71334
0.9459	High Similarity	NPC198826
0.9459	High Similarity	NPC188203
0.9459	High Similarity	NPC100887
0.9459	High Similarity	NPC324233
0.9459	High Similarity	NPC275722
0.9456	High Similarity	NPC62042
0.9456	High Similarity	NPC85131
0.9452	High Similarity	NPC15329
0.9452	High Similarity	NPC166036
0.9452	High Similarity	NPC12367
0.9452	High Similarity	NPC238279
0.9452	High Similarity	NPC131451
0.9452	High Similarity	NPC203077
0.9452	High Similarity	NPC118726
0.9448	High Similarity	NPC12377
0.9448	High Similarity	NPC226987
0.9448	High Similarity	NPC143903
0.9441	High Similarity	NPC284556
0.9441	High Similarity	NPC301178
0.9408	High Similarity	NPC295009
0.9408	High Similarity	NPC260640
0.94	High Similarity	NPC235165
0.94	High Similarity	NPC472916
0.94	High Similarity	NPC255106
0.9396	High Similarity	NPC167091
0.9396	High Similarity	NPC274327
0.9396	High Similarity	NPC183878
0.9396	High Similarity	NPC280937
0.9396	High Similarity	NPC231018
0.9396	High Similarity	NPC176775
0.9396	High Similarity	NPC88645
0.9396	High Similarity	NPC292214
0.9396	High Similarity	NPC206238
0.9396	High Similarity	NPC47781
0.9396	High Similarity	NPC255350
0.9396	High Similarity	NPC271779
0.9396	High Similarity	NPC69394
0.9396	High Similarity	NPC145379
0.9396	High Similarity	NPC22519
0.9396	High Similarity	NPC160951
0.9392	High Similarity	NPC256406
0.9392	High Similarity	NPC204515
0.9384	High Similarity	NPC239312
0.9384	High Similarity	NPC130230
0.9384	High Similarity	NPC119660
0.9384	High Similarity	NPC108406
0.9384	High Similarity	NPC275772
0.9384	High Similarity	NPC93034
0.9375	High Similarity	NPC471417
0.9342	High Similarity	NPC225624
0.9342	High Similarity	NPC285973
0.9342	High Similarity	NPC476980
0.9338	High Similarity	NPC472910
0.9338	High Similarity	NPC470402
0.9338	High Similarity	NPC48208
0.9338	High Similarity	NPC474208
0.9338	High Similarity	NPC474836
0.9338	High Similarity	NPC96167
0.9338	High Similarity	NPC245758
0.9338	High Similarity	NPC156057
0.9338	High Similarity	NPC162869
0.9338	High Similarity	NPC472911
0.9338	High Similarity	NPC222814
0.9338	High Similarity	NPC472914
0.9338	High Similarity	NPC472913
0.9338	High Similarity	NPC475267
0.9333	High Similarity	NPC208197
0.9333	High Similarity	NPC92659
0.9333	High Similarity	NPC44079
0.9333	High Similarity	NPC167815
0.9333	High Similarity	NPC26227
0.9333	High Similarity	NPC163780
0.9333	High Similarity	NPC128863
0.9333	High Similarity	NPC227325
0.9333	High Similarity	NPC214138
0.9333	High Similarity	NPC50715
0.9333	High Similarity	NPC2476
0.9333	High Similarity	NPC196439
0.9333	High Similarity	NPC201136
0.9333	High Similarity	NPC4455
0.9333	High Similarity	NPC280339
0.9333	High Similarity	NPC138360
0.9333	High Similarity	NPC183597
0.9333	High Similarity	NPC201451
0.9333	High Similarity	NPC113906
0.9333	High Similarity	NPC146165
0.9329	High Similarity	NPC120537
0.9329	High Similarity	NPC39732
0.9329	High Similarity	NPC161277
0.9329	High Similarity	NPC142540
0.9329	High Similarity	NPC199100
0.9329	High Similarity	NPC60972
0.9329	High Similarity	NPC101996
0.9329	High Similarity	NPC180234
0.9329	High Similarity	NPC39007
0.9324	High Similarity	NPC45873
0.9324	High Similarity	NPC306821
0.932	High Similarity	NPC194856
0.932	High Similarity	NPC276930
0.932	High Similarity	NPC119059
0.9315	High Similarity	NPC216314
0.9315	High Similarity	NPC195919
0.9315	High Similarity	NPC165389
0.9315	High Similarity	NPC120924
0.931	High Similarity	NPC142165
0.9281	High Similarity	NPC308992
0.9281	High Similarity	NPC258331
0.9276	High Similarity	NPC62518
0.9276	High Similarity	NPC215375
0.9272	High Similarity	NPC98661
0.9272	High Similarity	NPC245546
0.9272	High Similarity	NPC43243
0.9272	High Similarity	NPC247017
0.9272	High Similarity	NPC266960
0.9272	High Similarity	NPC49824
0.9267	High Similarity	NPC75279
0.9267	High Similarity	NPC250822
0.9267	High Similarity	NPC472915
0.9267	High Similarity	NPC276409
0.9262	High Similarity	NPC31363
0.9262	High Similarity	NPC251110
0.9262	High Similarity	NPC117579
0.9262	High Similarity	NPC171010
0.9262	High Similarity	NPC226973
0.9262	High Similarity	NPC260895
0.9262	High Similarity	NPC149614
0.9262	High Similarity	NPC308451

Chemically structural similarity: II. Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC10467 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	474
0.1-0.2	1012
0.2-0.3	1883
0.3-0.4	2628
0.4-0.5	1727
0.5-0.6	957
0.6-0.7	313
0.7-0.8	103
0.8-0.85	35
0.85-0.9	12
0.9-0.95	5
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9396	High Similarity	NPD2801	Approved
0.92	High Similarity	NPD1934	Approved
0.9178	High Similarity	NPD1511	Approved
0.9139	High Similarity	NPD2393	Clinical (unspecified phase)
0.9054	High Similarity	NPD1512	Approved
0.9021	High Similarity	NPD1510	Phase 2
0.8896	High Similarity	NPD3882	Suspended
0.875	High Similarity	NPD3818	Discontinued
0.8741	High Similarity	NPD943	Approved
0.8741	High Similarity	NPD1240	Approved
0.8693	High Similarity	NPD4380	Phase 2
0.8625	High Similarity	NPD6167	Clinical (unspecified phase)
0.8625	High Similarity	NPD6166	Phase 2
0.8625	High Similarity	NPD6168	Clinical (unspecified phase)
0.8621	High Similarity	NPD1607	Approved
0.8609	High Similarity	NPD4378	Clinical (unspecified phase)
0.859	High Similarity	NPD3817	Phase 2
0.8581	High Similarity	NPD1549	Phase 2
0.8535	High Similarity	NPD4868	Clinical (unspecified phase)
0.8514	High Similarity	NPD1550	Clinical (unspecified phase)
0.8514	High Similarity	NPD1552	Clinical (unspecified phase)
0.8491	Intermediate Similarity	NPD5494	Approved
0.8485	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.8466	Intermediate Similarity	NPD7054	Approved
0.8446	Intermediate Similarity	NPD2796	Approved
0.8415	Intermediate Similarity	NPD7472	Approved
0.8415	Intermediate Similarity	NPD7074	Phase 3
0.8385	Intermediate Similarity	NPD6232	Discontinued
0.8365	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.8364	Intermediate Similarity	NPD6797	Phase 2
0.8344	Intermediate Similarity	NPD7473	Discontinued
0.8322	Intermediate Similarity	NPD2935	Discontinued
0.8313	Intermediate Similarity	NPD7251	Discontinued
0.8299	Intermediate Similarity	NPD230	Phase 1
0.825	Intermediate Similarity	NPD7075	Discontinued
0.8247	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8239	Intermediate Similarity	NPD5402	Approved
0.8212	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.821	Intermediate Similarity	NPD1247	Approved
0.8182	Intermediate Similarity	NPD6799	Approved
0.8176	Intermediate Similarity	NPD7819	Suspended
0.8176	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD7808	Phase 3
0.8133	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD6801	Discontinued
0.8105	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.8063	Intermediate Similarity	NPD1465	Phase 2
0.805	Intermediate Similarity	NPD7411	Suspended
0.8036	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8024	Intermediate Similarity	NPD5844	Phase 1
0.8012	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7987	Intermediate Similarity	NPD6599	Discontinued
0.7987	Intermediate Similarity	NPD3750	Approved
0.7917	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7905	Intermediate Similarity	NPD3027	Phase 3
0.7898	Intermediate Similarity	NPD2532	Approved
0.7898	Intermediate Similarity	NPD2533	Approved
0.7898	Intermediate Similarity	NPD2534	Approved
0.7895	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7891	Intermediate Similarity	NPD9494	Approved
0.7879	Intermediate Similarity	NPD6959	Discontinued
0.7867	Intermediate Similarity	NPD1613	Approved
0.7867	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7866	Intermediate Similarity	NPD919	Approved
0.7843	Intermediate Similarity	NPD1551	Phase 2
0.7838	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7806	Intermediate Similarity	NPD2800	Approved
0.7805	Intermediate Similarity	NPD3749	Approved
0.7799	Intermediate Similarity	NPD920	Approved
0.7799	Intermediate Similarity	NPD5403	Approved
0.7785	Intermediate Similarity	NPD5401	Approved
0.7784	Intermediate Similarity	NPD3926	Phase 2
0.7778	Intermediate Similarity	NPD6559	Discontinued
0.7771	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.777	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7744	Intermediate Similarity	NPD7768	Phase 2
0.7738	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7707	Intermediate Similarity	NPD6190	Approved
0.7697	Intermediate Similarity	NPD447	Suspended
0.7692	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7677	Intermediate Similarity	NPD2344	Approved
0.7673	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7671	Intermediate Similarity	NPD9269	Phase 2
0.7662	Intermediate Similarity	NPD3748	Approved
0.7647	Intermediate Similarity	NPD6651	Approved
0.7619	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD2313	Discontinued
0.7616	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7593	Intermediate Similarity	NPD3226	Approved
0.7584	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7584	Intermediate Similarity	NPD2798	Approved
0.758	Intermediate Similarity	NPD1243	Approved
0.7547	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7545	Intermediate Similarity	NPD6234	Discontinued
0.7544	Intermediate Similarity	NPD3751	Discontinued
0.7532	Intermediate Similarity	NPD4628	Phase 3
0.7531	Intermediate Similarity	NPD1653	Approved
0.7514	Intermediate Similarity	NPD5953	Discontinued
0.75	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD7286	Phase 2
0.75	Intermediate Similarity	NPD7390	Discontinued
0.75	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7484	Intermediate Similarity	NPD2309	Approved
0.7455	Intermediate Similarity	NPD37	Approved
0.7453	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7452	Intermediate Similarity	NPD2346	Discontinued
0.7436	Intermediate Similarity	NPD2799	Discontinued
0.7429	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.74	Intermediate Similarity	NPD1203	Approved
0.74	Intermediate Similarity	NPD1470	Approved
0.7397	Intermediate Similarity	NPD9268	Approved
0.7391	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7389	Intermediate Similarity	NPD6099	Approved
0.7389	Intermediate Similarity	NPD6100	Approved
0.7371	Intermediate Similarity	NPD7685	Pre-registration
0.7368	Intermediate Similarity	NPD5242	Approved
0.7365	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7355	Intermediate Similarity	NPD1933	Approved
0.7353	Intermediate Similarity	NPD7199	Phase 2
0.7349	Intermediate Similarity	NPD6844	Discontinued
0.7329	Intermediate Similarity	NPD1548	Phase 1
0.7321	Intermediate Similarity	NPD4965	Approved
0.7321	Intermediate Similarity	NPD4966	Approved
0.7321	Intermediate Similarity	NPD4967	Phase 2
0.731	Intermediate Similarity	NPD3787	Discontinued
0.731	Intermediate Similarity	NPD5710	Approved
0.731	Intermediate Similarity	NPD5711	Approved
0.7297	Intermediate Similarity	NPD6781	Approved
0.7297	Intermediate Similarity	NPD6779	Approved
0.7297	Intermediate Similarity	NPD6782	Approved
0.7297	Intermediate Similarity	NPD6776	Approved
0.7297	Intermediate Similarity	NPD6778	Approved
0.7297	Intermediate Similarity	NPD6777	Approved
0.7297	Intermediate Similarity	NPD6780	Approved
0.7267	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD6832	Phase 2
0.7255	Intermediate Similarity	NPD4908	Phase 1
0.725	Intermediate Similarity	NPD2654	Approved
0.7248	Intermediate Similarity	NPD1201	Approved
0.7248	Intermediate Similarity	NPD1610	Phase 2
0.7241	Intermediate Similarity	NPD7228	Approved
0.7215	Intermediate Similarity	NPD7033	Discontinued
0.7215	Intermediate Similarity	NPD4308	Phase 3
0.7211	Intermediate Similarity	NPD9545	Approved
0.7205	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD9717	Approved
0.72	Intermediate Similarity	NPD3972	Approved
0.7192	Intermediate Similarity	NPD9493	Approved
0.7186	Intermediate Similarity	NPD6385	Approved
0.7186	Intermediate Similarity	NPD6386	Approved
0.7181	Intermediate Similarity	NPD7435	Discontinued
0.7178	Intermediate Similarity	NPD4357	Discontinued
0.7169	Intermediate Similarity	NPD7458	Discontinued
0.7167	Intermediate Similarity	NPD8150	Discontinued
0.7167	Intermediate Similarity	NPD8434	Phase 2
0.7161	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7161	Intermediate Similarity	NPD3268	Approved
0.7161	Intermediate Similarity	NPD3764	Approved
0.716	Intermediate Similarity	NPD5353	Approved
0.7143	Intermediate Similarity	NPD5536	Phase 2
0.7135	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7133	Intermediate Similarity	NPD422	Phase 1
0.712	Intermediate Similarity	NPD4360	Phase 2
0.712	Intermediate Similarity	NPD4363	Phase 3
0.7107	Intermediate Similarity	NPD2899	Discontinued
0.7095	Intermediate Similarity	NPD8312	Approved
0.7095	Intermediate Similarity	NPD8313	Approved
0.709	Intermediate Similarity	NPD7696	Phase 3
0.709	Intermediate Similarity	NPD7698	Approved
0.709	Intermediate Similarity	NPD7697	Approved
0.7086	Intermediate Similarity	NPD1608	Approved
0.7083	Intermediate Similarity	NPD8151	Discontinued
0.7078	Intermediate Similarity	NPD2861	Phase 2
0.7078	Intermediate Similarity	NPD3018	Phase 2
0.7063	Intermediate Similarity	NPD5406	Approved
0.7063	Intermediate Similarity	NPD5408	Approved
0.7063	Intermediate Similarity	NPD5404	Approved
0.7063	Intermediate Similarity	NPD5405	Approved
0.7059	Intermediate Similarity	NPD2797	Approved
0.7059	Intermediate Similarity	NPD4288	Approved
0.7053	Intermediate Similarity	NPD7871	Phase 2
0.7053	Intermediate Similarity	NPD7870	Phase 2
0.7051	Intermediate Similarity	NPD411	Approved
0.7037	Intermediate Similarity	NPD6823	Phase 2
0.7031	Intermediate Similarity	NPD7701	Phase 2
0.703	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6534	Approved
0.7027	Intermediate Similarity	NPD6535	Approved
0.7019	Intermediate Similarity	NPD7266	Discontinued
0.7011	Intermediate Similarity	NPD7229	Phase 3
0.7006	Intermediate Similarity	NPD6233	Phase 2
0.6994	Remote Similarity	NPD8166	Discontinued
0.6993	Remote Similarity	NPD1876	Approved
0.6993	Remote Similarity	NPD3225	Approved
0.6989	Remote Similarity	NPD4362	Clinical (unspecified phase)
0.6989	Remote Similarity	NPD4361	Phase 2
0.6982	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6979	Remote Similarity	NPD7584	Approved

Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data